graphical contents list -...
TRANSCRIPT
Tetrahedron Letters Vol. 54, Issue 33, 2013
Contents
COMMUNICATIONS
Optical Pd2+ sensing by rhodamine hydrazone ligands: different stoichiometries in aqueous/nonaqueous environments pp 4357–4361
Honglin Li, Jianfang Cao, Hao Zhu, Jiangli Fan*, Xiaojun Peng*
The triazolyl analogue of the trityl cation pp 4362–4364
Mohamed Oukessou, Yves Génisson*, Dounia El Arfaoui, Abdeslem Ben-Tama, El Mestafa El Hadrami, Remi Chauvin*
(CF3CO)2O
CH2Cl2, 0°C
CNN
N
N NN
Ph
Ph
N NN
Ph Nu-E
Nu
CNN
NNNN
Ph
NNN Ph
Ph
« trizyl cation » 10 examples
OH
CNN
NNNN
Ph
NNN Ph
Ph - EE = H, K, ZnEtNu = O-, N-, S-or C-nucleophile
tris(1,2,3-triazolyl)methanol
Nardokanshone A, a new type of sesquieterpenoid–chalcone hybrid from Nardostachys chinensis pp 4365–4368
Peng-Cheng Wang, Xin-Hui Ran, Huai-Rong Luo, Yi-Min Zheng, Yu-Qing Liu, Jiang-Miao Hu*, Jun Zhou*
O
OOH
H3CO
OO
OCH3
4347
Contents lists available at SciVerse ScienceDirect
Tetrahedron Letters
journal homepage: www.elsevier .com/ locate/ tet le t
Chemoselective oxidative hydrolysis of EWG protected a-arylamino vinyl bromides to a-arylamino-a0-bromoacetones pp 4369–4372
Vittorio Pace*, Laura Castoldi, María J. Hernáiz, Andrés R. Alcántara, Wolfgang Holzer
NBrPG
NOPG
BrCa(BrO)2 (2.0 equiv.)
PG = Ac, Moc, Boc, Ts, 4-NsR = H, Me, NO2, CN, F
R RMeCN-AcOH (5:2 v/v)
H2O, 0 °C, 1h
Environmentally benign process for the synthesis of 2,3-disubstituted benzo[b]thiophenes using electrophiliccyclization
pp 4373–4376
Seoyoung Kim, Nikesh Dahal, Tanay Kesharwani*
SMeCuSO4/NaX
EtOH, r.t.R
SR
XX = I, Br, ClR = aryl, vinly, alkyl, TMS,
Organic synthesis in deep eutectic solvents: Paal–Knorr reactions pp 4377–4379
Scott Handy*, Kevin Lavender
OR R'
OR"NR R'
CC/U80 C, 12h
H2NR"
R, R' = Me or Ph
Remarkable difference in fluorescence lifetimes of the crystalline states of dibenzoylmethanatoboron difluorideand its diisopropyl derivative
pp 4380–4384
Mirai Tanaka, Eisuke Ohta, Atsushi Sakai, Yuichi Yoshimoto, Kazuhiko Mizuno, Hiroshi Ikeda*
4348 Contents / Tetrahedron Letters 54 (2013) 4347–4355
Relative configuration of luminaolide pp 4385–4387
Norihito Maru*, Toshiyasu Inuzuka, Keita Yamamoto, Makoto Kitamura, Peter J. Schupp, Kaoru Yamada, Daisuke Uemura*
Synthesis and spectroscopic properties of 5-tert-butyl-3-(trifluoromethyl)phthalonitrile: a novel precursor for thesynthesis of phthalocyanines
pp 4388–4391
Łukasz Łapok*, Arkadiusz Gut, Maria Nowakowska
Diastereoselective construction of continuous all-carbon quaternary centers via intramolecular oxidativecoupling reaction
pp 4392–4396
Weiqing Xie*, Hexiang Wang, Feng Fan, Junshan Tian, Zhiwei Zuo, Weiwei Zi, Kun Gao*, Dawei Ma*
BnNNBn
OO
O
O
trans-2
BnN
O
NBn
O
OO
4
BnN
O
NBn
O
OO
cis-1NaHMDS, I2, THF
-78oC to rtLDA, I2, THF/HMPA
-78oC
An unexpected involvement of ethyl-2-cyano-2-(hydroxyimino) acetate cleaved product in the promotionof the synthesis of nitriles from aldoximes: a mechanistic perception
pp 4397–4400
Dharm Dev, Nani Babu Palakurthy, Nitesh Kumar, Bhubaneswar Mandal*
R1 NOH
DBU, DCM, rt, N2
RSO3XY
R1 = aromatic, aliphaticR = CH3-C6H4, 2-NO2-C6H4, 4-NO2-C6H4, 2, 4-diNO2-C6H4
R1 N
Contents / Tetrahedron Letters 54 (2013) 4347–4355 4349
An alternative reduction course of the spiroketal side chain of steroid sapogenins induced by the presence of a23E-benzylidene moiety
pp 4401–4405
Manuel A. Ramos-Enríquez, Margarita Romero-Ávila, Marcos Flores-Álamo, Martín A. Iglesias-Arteaga*
NaBH3CNAcOH
a) 5α, 25R; R1= H, R2 = CH3b) 5β, 25S; R1= CH3, R2 = H
O
O
R1
R2
AcOH
+
O
R1
OHR2
H
2
O
O
R1
R2
3
O
R1
OHR2
H4
1
normal course
abnormal course
over reduction
SM Products (Yield %)1a 2a (64) 3a (32) 4a (0)1b 2b (52) 3b(18) 4b (4)
A macrolactonisation approach to the cembrane carbocycle of bielschowskysin pp 4406–4408
Eugene G. Yang, Karthik Sekar, Martin J. Lear*
O
OOH
O
O
TBDPSO
Cl O
OO
OH
OHHH
OO
H
HO
OAcbielschowskysin (1)
1
4
10 11
8
C
O
OOH
O
O
TBDPSO
TBSO OH
I
12
1
4
10
11
8
12 H
-acylketene intermediate
predisposes conformationfor cyclization
β
Synthesis of novel glycopeptidomimetics via Nb-protected-amino alkyl isonitrile based Ugi 4C reaction pp 4409–4413
Basavalingappa Vasantha, Girish Prabhu, Hosmani Basavaprabhu, Vommina V. Sureshbabu*
PgHN
R1
NC R2 CHO H2N COOMeR3
PgHN
R1HN
NO
R2
COOMe
R3
OO
O O
OO
PgHN
R1HN
NO
R2
COOMe
R3
O
NHO
OBzBzO
BzO
BzOO
AcOAcO
AcON N
NOAc
PgHN
R1HN
NO
R2
COOMe
R3
O
5a-5c 6a 7a-7c
Sugar acid 1 Sugar acid 3Sugar acid 2
+ +
Pg1HN
R1HN
NO
R2
NHPg2O
R3
O
OAc
OAc
OAcOAc12a, b
Pg1HN
R1HN
NO
R2HN
O
R3
O
OAc
OAc
OAcOAc
ONHPg2
R4
13a, b
4
Ugi-4C reaction employing Nb-protected-amino alkyl isonitrile, amino acid ester, aldehyde, and glycosyl acid has resulted in novel glycosylatedpeptidomimetics. Further, the protocol has been extended for the synthesis of N,N0-orthogonally protected glycosylated peptidomimetics as well.
Iron-catalyzed indirect hydration of alkynes in presence of methanesulfonic acid pp 4414–4417
Jungmin Park, Jihee Yeon, Phil Ho Lee, Kooyeon Lee*
R1 R2
FeCl2 4H2O (5 mol%)MsOH (1.1 equiv.)
DCE, 60 oC R1 R2O
or R1 R2
O
R1, R2 = H, alkyl, aryl, halide 16 examples
49 - 96% yields
4350 Contents / Tetrahedron Letters 54 (2013) 4347–4355
Novel ring transformation of mesoionic oxazoles into 2(1H)-pyrazinones by the reaction with TosMIC pp 4418–4421
Ryosuke Saijo, Ken-ichi Kurihara, Kazuki Akira, Hidemitsu Uno, Masami Kawase*
N
OO
R2
R1COCF3
N
NR1
OR2
Ts
C, DBU
- CO2
TsCH2N O2,
An efficient synthesis of coumarin- and quinolone-annulated thiazole derivatives via ligand-free iron(III)-catalyzed coupling followed by acid-promoted condensation
pp 4422–4424
K. C. Majumdar*, Debankan Ghosh
X N
SO
X NH
BrO
(i) FeCl3 (10 mol%),DMF, 120 oC
OR
R+ Na2S.xH2O
ii) HCl, rt
X = O, NMe, NEtR = alkyl or aryl group
New synthesis of a selective estrogen receptor modulator using an enatioselective phosphine-mediated 2+3cycloaddition
pp 4425–4428
Debra J. Wallace*, Robert A. Reamer
MeO
O
O
MeO
O
O
2+3cycloadditon
HO
O
Cl
Cl
PL3
Development of a scalable synthesis of P7C3-A20, a potent neuroprotective agent pp 4429–4431
Jacinth Naidoo, Christopher J. Bemben, Shawn R. Allwein, Jue Liang, Andrew A. Pieper, Joseph M. Ready*
Contents / Tetrahedron Letters 54 (2013) 4347–4355 4351
Reagent-free synthesis of 2,3,4-polysubstituted tetrahydroquinolines: application to the formal synthesis of(±)-martinellic acid and martinelline
pp 4432–4434
Zhouting Rong, Qingjiang Li, Wenhan Lin*, Yanxing Jia*
NH
HN
HN
NNH
NH
HO2C
NHmartinellic acid
+Reagent free
THF, 60 °CNH2
R1
NH
NHR2
OR2
R1
R1
R2
12 examplesup to 98% yield
AlCl3–NaI assisted cleavage of polymer-bound esters with concomitant amine coupling and azido-reductivecyclization: synthesis of pyrrolobenzodiazepine derivatives
pp 4435–4441
Ahmed Kamal*, S. Prabhakar, Nagula Shankaraiah, Nagula Markandeya, P. Venkat Reddy, Vunnam Srinivasulu, Manda Sathish
H3CO
O
N
X
O
Y
Z
X = N3Y = CO2CH3 / CHOZ = H, OMs, OTs
O
n = 4,5
AlCl3-NaI
H3CO
O
N
X Y H
O
N
OR1
R2
n
O
n
n = 4,5Z
X, Y = NH-C=O / N=CHZ = H, OMs, OTs
Diversity Oriented Synthesis
SLE method
Facile chemoselective carbonyl allylation of chalcones with allyltributylstannane catalyzed by CuI pp 4442–4445
Pabitra Kumar Kalita, Prodeep Phukan*
O
R2R1
OH
R2R1SnBu3
CuI (25 mol %),K2CO3
DMF, 70 oC+
R1 = H, Cl, F, Br, OMe, Me, Me2N etc.; R2 = H, F
A new isoluminol reagent for chemiluminescence labeling of proteins pp 4446–4450
Alessandro Palmioli, Marco Crisma, Cristina Peggion, PierNatale Brusasca, Davide Zanin, Andrea Dal Corso, Paolo Ingallinella,Francesco Peri*
4352 Contents / Tetrahedron Letters 54 (2013) 4347–4355
A facile and convenient way to functionalized trifluoromethylated spirocyclic[indole-3,4-pyrano[2,3-c]pyrazole]derivatives
pp 4451–4455
Xiaoqing Liu, Xiaoling Xu, Xu Wang, Wenxin Yang, Qun Qian, Min Zhang, Liping Song*, Hongmei Deng, Min Shao
N
O
OCN
R3F3C OEt
O OR1
R2
PiperidineEtOH, ref
R1 = H, Cl, Br, CH3, NO2 R2 = H, CH3 R3 = CN, CO2EtCONH2
R4 = H, Ph
1 2 3 4 5
+ + + R4-NHNH2
N
O
R1
R3
H2N
O
NN
CF3
R2
R4
Luminescent molecular solar concentrators made of multi-Bodipy dyes pp 4456–4462
Antoine Mirloup, Pascal Retailleau, Raymond Ziessel*
N N
S
O
B
O
O
O
O
I
N B NF F
S
SNN
S
B
O
O
O
O
S
OO
O
Direct conversion of glycerol into formic acid via water stable Pd(II) catalyzed oxidative carbon–carbonbond cleavage
pp 4463–4466
Prasanna Pullanikat, Joo Ho Lee, Kyung Soo Yoo, Kyung Woon Jung*
HO OHOH Pd(II) Catalyst
N
N
O
N
OMe
ClPd
CH3
H2O2, 60 oC61%
HCO2H
Construction of functionalized tricyclic dihydropyrazino-quinazolinedione chemotypes via an Ugi/N-acyliminiumion cyclization cascade
pp 4467–4470
Steven Gunawan, Christopher Hulme*
F O
OH
NO2
CNOEt
OEt
NH2
MeO OMeR1
CHO R2NH2
NHN
OEt
F
NO2
O R1
O
OEt
MeO OMe
MeOHN
NN
HN
OO
R1
R2H
HR3
R4
24 (+)
R3Br
R4Cl
Herein, we report the production of a diversified tricyclic scaffold in 3 synthetic operations involving an Ugi multicomponent reaction followed by an N-acyliminium ioncyclization cascade. Further functionalization of the biologically appealing tricyclic core 24 was achieved via sequential N-alkylation and N-acylation and/or sulfonation.
Contents / Tetrahedron Letters 54 (2013) 4347–4355 4353
Toward the chemoenzymatic synthesis of heparan sulfate oligosaccharides: oxidative cleavage of p-nitrophenylgroup with ceric ammonium salts
pp 4471–4474
Chao Cai, Lingyun Li, Cate Harvey, Jian Liu, Robert J. Linhardt*
Solid-supported ortho-iodoarylboronic acid catalyst for direct amidation of carboxylic acids pp 4475–4478
Nicolas Gernigon, Hongchao Zheng, Dennis G. Hall*
BOHHO
I
ONH
R1 OH
O
+H2NR2
(1.1 equiv)
(1.0 equiv)
14 (10 mol%)
4A mol. sievesCH2Cl2, rt
R1 NHR2
O
amide product
Odouble
evaporation
recyclable catalyst 14
4A m.s.
New strategy toward the diverted synthesis of oxidized abietane diterpenes via oxidation of 6,7-dehydroferruginolmethyl ether with dimethyldioxirane
pp 4479–4482
I. Córdova-Guerrero*, Lucía San Andrés, Alma E. Leal-Orozco, José M. Padrón, J. M. Cornejo-Bravo, Francisco León*
H
OMe
11
H
OMe
OHOH
H
OMe
O
12 15
DMDO DMDO
Highly efficient synthesis of aryl and heteroaryl trifluoromethyl ketones via o-iodobenzoic acid (IBX) pp 4483–4486
Huicheng Cheng, Yu Pei, Faqiang Leng, Jingya Li, Apeng Liang, Dapeng Zou*, Yangjie Wu, Yusheng Wu*
Ar CF3
O
Ar CF3
OH
Ar CF3
OH
Ar
O (1) cat. K2CO3 / DMF, rt
(2) H3O+ or TBAFH
+I
O
O
OHO+I
O
O
OH
(1) EtOAc; reflux
(2) Filtration
(IBX) (IBA)
+ Si CF3
Oxone
35 ExamplesUp to 99% YieldsRecylable Oxidant
4354 Contents / Tetrahedron Letters 54 (2013) 4347–4355
TiCl4 mediated preparation of (E)-non-conjugated homoallylic alcohols with a-substituted allylsilanes pp 4487–4490
Aymara M. M. Albury, Michael P. Jennings*
Me3Si
RR = Ph or C6H13
R'
OH
R
TiCl4R'CHO
E/Z : 8-20/1
2-Arylvinylpyrimidines versus 4-arylvinylpyrimidines: synthesis and comparison of the optical properties pp 4491–4496
Sylvain Achelle*, Françoise Robin-le Guen
N N
EDG
N N
EDG
Versus
Fluorescence
Halochromism
EmissionSolvatochromism
*Corresponding authorSupplementary data available via SciVerse ScienceDirect
Abstracted/indexed in: AGRICOLA, Beilstein, BIOSIS Previews, CAB Abstracts, Chemical Abstracts, Chemical Engineering andBiotechnology Abstracts, Current Biotechnology Abstracts, Current Contents: Life Sciences, Current Contents: Physical,Chemical and Earth Sciences, Current Contents Search, Derwent Drug File, Ei Compendex, EMBASE/Excerpta Medica, Medline,PASCAL, Research Alert, Science Citation Index, SciSearch. Also covered in the abstract and citation database SciVerse Scopus�.Full text available on SciVerse ScienceDirect�
Available online at www.sciencedirect.com
ISSN 0040-4039
Contents / Tetrahedron Letters 54 (2013) 4347–4355 4355